tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate

Base Information

Chemical Name:tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate
CAS No.:1287228-26-5
Molecular Formula:C₃₀H₄₉NO₄
Molecular Weight:487.723
Hs Code.:

Synonyms:tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate

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Chemical Property of tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate

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Technology Process of tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate

There total 5 articles about tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

: 1120-36-1
1-tetradecene

: 1287228-23-2
tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

: 1287228-26-5
tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 45 ℃; for 18h; Sealed vessel; Inert atmosphere;
DOI:10.1039/c0ob00643b

Reference yield:

: 1287228-19-6
(S)-tert-butyl 4-((S,Z)-1-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1287228-26-5
tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate

Guidance literature:: Multi-step reaction with 5 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

3: iron(III) chloride adsorbed on silica gel / chloroform / 12 h / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine / tetrahydrofuran / 16 h / 55 °C / Inert atmosphere

5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / 45 °C / Sealed vessel; Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron(III) chloride adsorbed on silica gel; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1039/c0ob00643b

Reference yield:

: 1287228-20-9
(S)-tert-butyl 4-((S,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1287228-26-5
tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate

Guidance literature:: Multi-step reaction with 4 steps

1: dmap; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2: iron(III) chloride adsorbed on silica gel / chloroform / 12 h / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine / tetrahydrofuran / 16 h / 55 °C / Inert atmosphere

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / 45 °C / Sealed vessel; Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron(III) chloride adsorbed on silica gel; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1039/c0ob00643b